Acetonitrile → 3,4-Bis-(1,1-dimethyl-prop-2-ynyloxy)-xanthen-9-one
反応式
[OH:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6](=[O:17])[C:7]3[C:12]([O:13][C:14]=2[C:15]=1[OH:16])=[CH:11][CH:10]=[CH:9][CH:8]=3.Cl[C:19]([CH3:23])([CH3:22])[C:20]#[CH:21].N12CCCN=[C:30]1[CH2:29][CH2:28][CH2:27]CC2.[C:35](#N)C>>[CH3:22][C:19]([CH3:23])([O:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6](=[O:17])[C:7]3[C:12]([O:13][C:14]=2[C:15]=1[O:16][C:29]([CH3:30])([CH3:35])[C:28]#[CH:27])=[CH:11][CH:10]=[CH:9][CH:8]=3)[C:20]#[CH:21]参加物
反応条件
- 温度
- 75 °C
実験手順
A solution of 3,4-dihydroxy-xanthen-9-one (1.25 g, 5.47 mmol), cupric chloride (30.2 mg, 0.225), 3-chloro-3-methyl-1-butyne (3.36 mL, 29.9 mmol), 1,8-diazabicyclo[5.4.0]undec-7-ene (2.00 mL, 13.3 mmol), and acetonitrile (100 mL) was stirred at room temperature for 11 h under argon. The solution was then heated at 75° C. for 2 h and cooled to room temperature. The solution was partitioned between ethyl acetate (100 mL) and water (75 mL). The ethyl acetate layer was dried over sodium sulfate and was concentrated by rotary evaporation. The product was purified by flash column chromatography (10:1 hexanes/ethyl acetate) to yield 496 mg (25%) of the title compound as a light yellow solid. 1H NMR (CDCl3, 300 MHz): δ 8.33 (dd, J1=7.97 Hz, J2=1.65, 1H), 8.07 (d, J=9.06 Hz, 1H), 7.71 (ddd, J1=8.18 Hz, J2=7.08, J3=1.58, 1H), 7.65 (d, J=9.06 Hz, 1H), 7.52 (dd, J1=8.52 Hz, J2=0.55, 1H), 7.38 (m, 1H), 2.66 (s, 1H), 2.30 (s, 1H), 1.84 (s, 6H), 1.77 (s, 6H).
後処理
- temperaturecooled to room temperature
- customThe solution was partitioned between ethyl acetate (100 mL) and water (75 mL)
- dry with materialThe ethyl acetate layer was dried over sodium sulfate
- concentrationwas concentrated by rotary evaporation
- customThe product was purified by flash column chromatography (10:1 hexanes/ethyl acetate)
出典と根拠
- ORDレコード
- ord-d7f4fc90fad34e528c2636322cc83446
- 出典データセット
- uspto-grants-2009_09
- 特許番号
- US07592143B2
反応ノート
読み込み中…